Therapeutically-valuable compounds of the quinin group.



PAUL rrfissmofnesnnswnzn y m PBASLE, or

assxcnon TO scorer! or cnnnican INDUSTRY rese .swrrznanenn.

'rmunu'rrcatnr-venuantn c'omrotmnsor THE mm ennui.

1,261,235. No Drawing.

To all whom it may concern.-

Be it known that I, Dr. Med. PAUL Hiissx, a citizen of the Swiss Republic, and resident of Basel, Switzerland, have invented new Therapeutically-Valuable Compounds hydroquinin, ethylhydrocuprein, to interact 1 in molecular. proportions, in some cases in presence of a suitable solvent or diluent, with C-C-diallylbarbituric acid in. the form either of the free acid orof asalt' thereof.

The new compounds are pronounced labor stimulants, extraordinarily reliable and powerfully active, which at the same time produce a desirable sedative and restful efl'ect.

The invention is illustrated by .the following examples: Example 1: A mixture of 65 grams of anhydrous quinin base, 41.6 grams of 0-0- diallylba'rbituric' acid and 200 grams of anhydrous methyl alcohol is boiled in. a reflux aparatus for half an.'hour. somewhat'prolonged standing the qulnmdiallylbarbituric acid separates in needle shaped crystals which melt at128 C. and

dissolve in water with some difiiculty, easily in ethyl alcohol, methyl alcohol and acetic ether, but notin petro and 39.09 per cent. of diallylbarbituric acid. Example 2: 65 grams of anhydrous qumin base and 41.6 grams of C-C-diallylbarbitpric acid are melted together for .some time.

The, viscous mass is recrystallized from acetic ether, the compound obtalned being identical with the product of Example 1.

Example3: 33.6 grams of; anhydrous hydroquinin base are melted'w1th20.08 grams of diallylbarbituric acid on a paraffin-bath and the product of reaction 1s recrystallized from alcohol. The hydroqulnin-diallylbarbituric acid thus obtainedis a white crystalline powder, melting at 104; and dissolving easily in the. usual orgamc solvents and difiicultly in cold-water.

Specification of Letters l'atent. Application filed May 26, 1917. Serial No. 171,242.

. the usual organic After the quinin group,

eum ether. lihe newcompound contains 60.91 per cent.'of qumm Manam 2," was.

Example 4: 39.6 grams of euquinin are melted with 20.08 grams of diallylbarbituric acid on reaction is recrystallized from alcohol. The

euq uinin barbituric acid thus obtained is a white, crystalline mass melting at 79 C. It dissolves easily in alcohol, chloroform and benzene and diflicultly inywater.

Example 5: 29.4 20.08 grams of diallylbarbituricacid and 120 grams of benzene are boiled in a reflux apparatus for half an hour. After cooling, the cinchonin-diallylbarbituric acid separates in the form of a white crystalline mass melting at 217 C. It is easily soluble V solvents and difiicultly 1n water.

Example 6: 34 grams of ethylhydrocuprein, 20.08 grams of diallylbarbituric acid and 150 grams of anhydrous alcohol are boiled in a reflux' apparatus for half an hour. After somewhat prolonged standing the ethylhydrocuprein-barbituric acid separates in fine needle shaped crystals. The new compound meltsat 135 0., is soluble in the usual organic solvents, but difilcultly soluble in water.

What I'claim' is I 1.- As new products the herein described therapeutically valuable compounds of (3-6- diallylbarbituric acid and alkaloids I of constituting well crystallized substances capable of being melted, diflicultlysoluble in water and easily soluble in ethyl alcohol, methyl alcohol, and acetic ether, but not soluble in'petroleum ether.

2. As .aynew'article of manufacture, the herein described therapeutically valuable eompound derived from quinin and diallyl-' barbituric acid, which constitutes a 'white crystalline substance i melting at 128 (3., difiicultly soluble in wateljy'easily soluble in ethyl alcohol, methyl alcohol and acetic ether, but insoluble etroleum ether.

In witness whereo I have hereunto signed my name this 5th day ofMay, 1917, in the presence of two subscribing witnesses.

DRQ'MED. HllSSY. Vlfitiaasses 0 ARL PAUM'ER, Arum) Rn'mn.

a parafiin bath and the product ofams of cinchonin, 

